Illustrations by Peter Arkle

COURTING A CO-ED CRUSH
Entwine
765 Washington St., nr. W. 12th St.; 212-727-8765
A West Village date bar within fist-pumping distance of Cielo and Kiss & Fly, but with a far more mature atmosphere (and unintrusive soundtrack). Start in the first-floor garden, then slide into the darker, sexier lower level if things are going well.

IMPRESSING A FIRST DATE
Bill’s Place
148 W. 133rd St., nr. Seventh Ave.; 212-281-0777
Jazzman Bill Saxton’s narrow brownstone club epitomizes New York cool. Its building hosted Billie Holiday’s first gigs and now it’s a BYOB hangout for working musicians. Hit the Friday midnight show, a raucous bebop session stretching to early morning.

PROPOSING MARRIAGE
Bar Pleiades
20 E. 76th St., nr. Madison Ave.; 212-772-2600
Talk about memorable: At Daniel Boulud’s uptown charmer, the deep banquettes are surrounded by creamy, quilted walls that will make your beloved feel like she (or he) is luxuriating in a Chanel purse. Assuming you get a yes, the Surrey Hotel’s romantic suites are just an elevator ride away.

BACHELOR PARTY
Happy Ending
302 Broome St., nr. Forsyth St.; 212-334-9676
This purposefully sleazy former massage parlor boasts a debauched crowd, a party-fueling soundtrack, and repurposed sauna rooms that double as semi-private nooks. The bar may be known for its tame weekday readings, but late nights in the basement, anything goes.

FIRST-YEAR ANNIVERSARY
The Bar Room at the Modern
9 W. 53rd St., nr. Fifth Ave. 212-333-1220
Danny Meyer’s elegant, unstuffy museum eatery is a splurge-worthy venue for some mutual back patting. Gaze at the wall-length forest mural, and dream of the dinners you’ll host at your house upstate in just five years if you stick with it.

CELEBRATING CHILDBIRTH
Rye
247 S. 1st St., nr. Havemeyer St., Williamsburg 718-218-8047
Toast the new arrival at a laid-back boîte with prices—a pork-belly sandwich is $8—that won’t require a dip into the college fund. The sherry-accented Havemeyer ($10) is a fine gateway beverage for ex-PBR guzzlers suddenly thrust into adulthood.

EXTRAMARITAL TRYST
Covet
137 E. 55th St., nr. Lexington Ave.; 212-223-2829
This new bi-level lounge is dark, dripping with fur, and the last place anyone would look for a happily married zhlub. Cerebral cocktails by mixologist Orson Salicetti will lessen the sleaze factor, and if you’re feeling particularly paranoid, there’s a private alcove with mirrored ceiling.

REKINDLING ROMANCE
Mayahuel
304 E. 6th St., nr. Second Ave. 212-253-5888
Tuck yourselves into a bright, Mexican-tiled corner on the second floor, enjoy artisanal drinks like the pepper-infused Sinaloa Cobbler, and let the honeymoon memories wash over you—all while bathed in the kind of soft lighting that erases the ravages of time.

POST-DIVORCE-REBOUND PARTY
Provocateur
18 Ninth Ave., nr. 13th St. 212-929-9036
On the prowl with money to burn before the settlement goes through? Spring for a table at this sexed-up tank for the rich attached to the Hotel Gansevoort. Bottles are exorbitant (think $500), but they’re a predictably effective lure for the young and beautiful.

Related:

• Articles by Joshua David Stein
• Table of Contents: May 24, 2010 issue of New York | Subscribe!